101 Deep Questions to Ask Friends to Get to Know Them Better
February 3, 2025
In today’s world of social media and constant news, it’s often challenging to find the mental space to genuinely connect with each other. But maintaining healthy relationships is an essential pillar for both our personal and professional lives, and if the relationship is worth keeping, it doesn’t require too much of us. It can all start with a simple question (Scroll down for 101 Deep Questions to Ask Friends to Get to Know Them Better).
Yet it’s also surprising to consider that some of the people closest to us are actually people we might not be fully aware of or truly know. This is prevalent: the incessant stream of work, family, household maintenance, hobbies, exercise, and you name it can all get in the way. There is always something calling our attention, even if it’s that Instagram reel or news article that popped up two seconds ago. But like any existing relationship, friendships cannot grow if they’re neglected. And if you’re more inclined to stick to the usual small talk, that’s fine if the friendship is not particularly significant to you. Though if it is, and it’s been a while since you and your friend let your guards down, why not consider asking them questions that go beyond how are you?
Follow along for 101 deep questions to ask your friends to get to know them better. Below you’ll find fun questions to ask friends, deeper questions to ask friends, difficult questions to ask friends and questions about your own friendship. Chances are you’ll hear an answer you’ve never heard from them before. After all, no matter how long you’ve known somebody, it’s impossible to know everything about them. You might even catch yourself wondering how you’d answer some of these questions if you asked them to yourself.
Deep Questions to Ask Friends to Get to Know them Better
Fun Questions to Ask Your Friends
Expressing your curiosity about friends demonstrates that you value their opinion. It can start with questions you might have asked your friends when you were little. And what’s wrong with that? Sure, some of these questions might be ones you hear children asking each other, but there’s a point to the innocence. The simple, fun questions are often the ones we’ve forgotten–or dismissed–over time, when they’re a great way to connect us to ourselves again.
1) Who is your greatest role model?
2) If you could time travel to any era, which one would you choose?
3) What is your biggest pet peeve?
4) What famous person do you think you would be best friends with?
5) Are you a dog or cat person?
6) Who would you invite to your dream dinner party?
7) Where is the best place you’ve ever visited?
8) If you weren’t in your current profession, what would you be doing?
9) Who is your celebrity crush?
10) What’s your favorite childhood memory?
Deep Questions to Ask Friends (Continued)
11) What is the most exciting adventure you have been on?
12) What is your favorite memory?
13) What does your ideal weekend with friends look like?
14) What is something on your bucket list?
15) What are three places you want to go to before you die?
16) If you could have a different name, what would it be?
17) If you could keep any animal as a pet, which would you choose?
18) What’s your favorite unusual food combination?
19) What’s one reality show you would consider being a contestant on?
20) Do you prefer calls, texts or video chats?
List (Continued)
21) Describe your perfect day.
22) Which book or movie influenced you the most growing up?
23) Is there a movie or show you could watch on repeat?
24) What was your favorite game to play as a kid?
25) What movie or show would you never see again?
Deeper questions to ask friends
As we head to the deeper end, consider some questions that you hadn’t had a chance to ask your friends but had always wanted to know. Friendship dynamics inevitably change from new life paths taken, living in different cities or lack of communication. But a way to strengthen that foundation of trust, safety and respect for you and your friends is to be open. Many people will struggle with how open they can be, and you’ll find some friends–perhaps even yourself–wanting to veer away from answering some of them. Because deeper questions have the power to bring you closer together through vulnerability.
26) What is your earliest memory?
27) What makes your life feel purposeful?
28) Do you think you’ve met your soulmate?
29) If one wish of yours could come true, what would it be?
30) What is the best piece of advice you’ve ever been given?
Deep Questions to Ask Friends (Continued)
31) What values are important to you?
32) Do you care about how others see you?
33) If one wish of yours could come true, what would it be?
34) What brings you joy?
35) If you could travel anywhere, where would you go?
36) If you could meet anyone in the world, alive or deceased, who would it be?
37) What would you like to accomplish in life?
38) If you could leave a “mark on the world” that preceded you, what would it be?
39) Looking back on your life, who or what makes you instantly light up?
40) What is the most trouble you’ve ever been in?
List (Continued)
41) Is there a time when you did something that seems so out of character that most people wouldn’t believe it?
42) Who sticks out as being an early positive influence in your life?
43) Who in your family do you struggle with?
44) Who are you most like in your family?
45) Who is most important to you now?
46) Did you grow up in an emotionally supportive environment?
47) How did you feel about where you grew up?
48) What keeps you up at night?
49) What do you need more of in your life?
50) What really frustrates you?
Deep Questions to Ask Friends (Continued)
51) What do you need less of in your life?
52) What do you really care about?
53) What do you feel has been your greatest “win” so far in life?
54) What three words describe what you’re most grateful for?
55) How do you cope when things get hard?
56) How do you like to receive care?
57) Would you rather people perceive you as being kind, smart or attractive?
58) What do you want people to know about you?
59) What’s been on your heart and mind recently?
60) What are you still hoping to accomplish?
61) What are your current priorities in this season of your life, and why?
62) What is your greatest accomplishment?
63) What kind of person do you want to be in the world?
64) If you had a whole day where you could do anything you wanted, what would you do?
Difficult questions to ask friends
If you’ve made it this far down the list, then your friendship is probably one that doesn’t shy away from discomfort. As many of us know, friendships, and other social relationships, can deteriorate when people only show how they are thriving. The caricatured facade comes across as exhausting to present and relate to not only because it’s an inaccurate, deliberate portrayal of life but because there’s no room for authenticity. It’s often easier to pretend like everything is fine, when doing so prevents any growth. That’s where some difficult questions come in.
65) What’s one bad habit you wish you could quit?
66) Do you recall your nightmares? Do you get nightmares often?
67) If you found money on the ground, would you keep it or look for the owner?
68) What is your biggest regret?
69) How long does it take to earn your trust?
70) How do you know when you can trust someone?
Deep Questions to Ask Friends (Continued)
71) What do you think other people notice first about you?
72) Has a friend ever stopped talking to you?
73) What made that friendship come to an end?
74) Did you ever stop talking to a longtime friend?
75) What made you stop talking to them?
76) If you lost your job or home, would you come to me for help?
77) If you lost a loved one, would you come to me for comfort or support?
78) Can you name an event that had a significant impact on your life?
79) What is your relationship with your parents like?
80) What is your greatest fear?
81) Do you have a particular memory you would love to forget?
82) Do you experience anxiety often?
83) What is something most people would never know about you?
84) What holds you back from opening up about that?
85) What is the most difficult part of your life right now?
86) How do you know if you can trust someone?
87) What had the greatest impact on your life?
Questions to ask friends about your own friendship with them
As a healthy friendship thrives on reciprocity, why not ask your friend questions about the two of you? It’s one thing to know how your friend would respond to questions about themselves. It’s a whole other when you center the relationship that runs between you both. If you haven’t had the chance to ask some of these questions to your friend directly, maybe you’ve thought about them on your own. So why not give it a go and find out yourself?
88) If we could only do one thing together before we die, what would it be?
89) What about our friendship is important to you?
90) What qualities do you look for in a friend?
Deep Questions to Ask Friends (Continued)
91) What do you value most in a friendship?
92) What qualities do you look for in a partner?
93) In what ways do you feel supported in the friendship?
94) Have you ever kept a secret from me?
95) What made that secret difficult to share?
96) In which ways do you not feel supported in our friendship?
97) Is there anything I can do to show my appreciation for your friendship that I do not already do?
98) How do you feel trusted in our friendship?
99) What is your favorite thing about me?
100) What do you look forward to doing together?
101) What is your favorite part about our friendship? And is there something you wish we could have more of in our friendship?
The questions we ask our friends and the questions we ask of ourselves
Sometimes strengthening the relationships we already have can feel more uncomfortable than maintaining them as they are. The questions listed above might feel like awkward icebreakers with friends only because we haven’t yet had a chance to sit down and ask the questions we’d want them to ask us. It just takes one person to help open the door to a stronger friendship, and it requires the other party to want to step inside. So what’s stopping you from making some time in your busy schedule to ask some of these questions to your friends? Try putting the phone down and get together. Meaningful relationships require effort, and this is a good start.
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